Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F10%3A63509363" target="_blank" >RIV/70883521:28110/10:63509363 - isvavai.cz</a>

Výsledek na webu

—

DOI - Digital Object Identifier

—

Jazyk výsledku

angličtina

Název v původním jazyce

Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

Popis výsledku v původním jazyce

A comparative study for selective glucosylation of N-unsubstituted 4 hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl--D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl--D-glucopyranosyl bromide, -D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl--D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl--D-glucopyranosyl bromide with Cs2CO3in CH3CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl--D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl--D-glucopyranosyloxy)quinolin-2(1H)-oneswere deacetylated into 4-(-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et3N in MeOH. In some instances the deacetylation was accompanied by the sugar?aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon

Název v anglickém jazyce

Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

Popis výsledku anglicky

A comparative study for selective glucosylation of N-unsubstituted 4 hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl--D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl--D-glucopyranosyl bromide, -D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl--D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl--D-glucopyranosyl bromide with Cs2CO3in CH3CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl--D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl--D-glucopyranosyloxy)quinolin-2(1H)-oneswere deacetylated into 4-(-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et3N in MeOH. In some instances the deacetylation was accompanied by the sugar?aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2010

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Carbohydrate Research

ISSN

0008-6215

e-ISSN

—

Svazek periodika

345

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

—

Kód UT WoS článku

—

EID výsledku v databázi Scopus

—